Chicago knows how to wine down.
From cozy neighborhood cafés to buzzy new hotspots, the city is full of places pouring midweek deals worth toasting to. Whether you’re craving a half-priced bottle with dinner or a patio hang with friends, these Wine Wednesday specials make hump day a whole lot smoother.
Photo via Facebook / Brasero Chicago
1709 W Chicago Ave. - West Town
One of Chicago’s hottest new restaurants, Brasero spotlights bold South American flavors and an award-worthy wine list. Right now Wednesdays mean 50% off bottles, an easy way to explore their 100+ South American selections under $100 while feasting on shareable bites, steaks, and seafood. Prefer to bring your own? They allow it with a $60 corkage fee (just make sure it’s not already on their list).
Photo via Instagram / ambar_restaurantchicago
700 N Clark St. - River North
Ambar brings bold Balkan flavors to the table, and Wednesdays make it even better: half-price bottles of wine (with dinner) to reward yourself for making it halfway through the week. Whether you go à la carte or dive into their unlimited dining, it’s the perfect midweek sip ‘n’ savor.
Photo via beitychicago.com
813 W Fulton St. - West Loop
Beity serves up a fresh spin on Lebanese eats in the heart of Fulton Market. On Wednesdays, bottles of wine are half-off—ideal for pairing with mezze, or street food favorites. While you’re at it, be sure to indulge in one of their “Lebanese pantry”-inspired cocktails from the mind of Beity’s Beverage Director, and Michelin Exceptional Cocktail Awardee, Olivia Fadden.
Photo Via Facebook / Easy Does It
2354 N Milwaukee - Logan Square
Take it easy any day of the week at this laid-back Logan wine bar, shop, and hang-out. Happy hour is all night Monday; Tuesday–Friday, 5–7pm; Saturday & Sunday, 12–2pm. $32 bottles, $8 glasses, $3 beers, plus no- and low- options mean there's a little something for the whole crew to enjoy.
Photo via Facebook / Sochi Saigonese Kitchen
1358 W Belmont Ave. - Lake View
This husband-and-wife team brings vibrant Saigonese flavors to Chicago with plenty of heart. Wednesdays mean all-day happy hour, featuring $30 wine bottles and $10 cocktails. It's a perfect excuse to sip while you snack your way through their bold, flavorful dishes.
Photo via Facebook / The Monkey's Paw Chicago
2524 N Southport Ave. - Lincoln Park
A Lincoln Park staple since 2012, The Monkey’s Paw is known for its cozy vibe, serious whiskey list, and boutique wines. On Wednesdays, every bottle of wine is half-off—no exclusions—making it the perfect midweek spot to sip something special and stay awhile.
Photo via Facebook / Flo & Santos
1310 S Wabash Ave. - South Loop
This South Loop favorite mixes Polish comfort food, Italian classics, and tavern-style pizza in a laid-back pub setting with a big patio. On Wednesdays, they’ve got half-off bottles of wine, perfect for pairing with pierogies, pork wings, or a post-game slice.
Photo via Facebook / Cafe Yaya Chicago
2431 N. Lincoln Ave. - Lincoln Park
A laid-back neighborhood cafe with serious charm, Cafe Yaya does it all—pastries and coffee by day, Mediterranean- and French-inspired plates by night. Their daily Golden Hour (2–5pm) draws crowds for $10 cocktails and half-off pastries, but Wednesdays are all about the wine: every bottle is half-off. Bonus points—it’s the little sibling to acclaimed Galit right next door.
Photo via Instagram / Meslerkitchenbarlounge
1401 E 53rd St. - Hyde Park
This New American restaurant, bar, and lounge was made for mingling. It's open daily for bunch, lunch, and dinner—but swing by Tuesday–Thursday between 3–5pm for $8 house wines, $5 beers, and a rotating $10 bartender's choice.
Photo via turquoisedining.com
2147 W Roscoe St. - Roscoe Village
Roscoe Village’s go-to for Turkish and Mediterranean flavors, Turquoise has been serving the neighborhood since 2002. Think mezze spreads, grilled meats, and plenty of warm hospitality. On Wednesdays, every bottle of wine is half-off. Not a bad excuse to linger a little longer over that extra plate of hummus or baklava...
Photo via Facebook / Chief O’Neill’s Pub Restaurant Garden Event Space
3471 N Elston Ave. - Avondale
An Irish pub classic since 1999, Chief O’Neill’s is as much about the cozy pints and live music as it is about the sprawling garden patio. Wednesdays mean half-off wine bottles all day, plus half-price apps from 4–6pm. It's ideal for a midweek hang that feels a little like a mini-vacation across the pond.
Did we miss your favorite spot? Let us know!
